I tried to stifle the old flame but it keeps roaring back
This is probably as cliche as it's likely to get.
I fell in love with my best friend in college. We had classes together, and were both involved in the theatre. We spent time together doing a few shows, and hanging out afterwards. Whenever I could drum up the courage, I would insinuate that I would like to spend time with him one-on-one and occasionally we did, but usually in groups with our mutual friends.
My senior year (fourth year, I spent six in college) he was finishing up his masters degree and I was terrified he would graduate and disappear. We were in the middle of a show where there was a lot of pairing off - I think five or six couples sprang up behind the scenes. After the cast party I told him how I felt about him. He was very kind and understanding, but turned me down, saying he was 'flattered', but did not feel the same. We agreed to stay friends, and have done so since then, even after we both graduated. Since then our contact has been sporading, sometimes going six months to a year without contact. And even though I told him I would, I've not yet been able to get over him.
Every so often one or both of us will sent an SOS, saying how much we miss each other and we'll get together. We see a lot of movies, go to plays or musicals. In January I went to see a show with my sister and ran into him there. This is where things start to get strange.
He was with another girl, one of our mutual friends, but he's not dating her. He spent most of the night talking to me. Since then we've been much more involved with each other, rarely going more than a week without speaking, which is very strange. This month he's invited me out four times. Usually they're very vague requests, but recently they've started to sound more and more like dates.
"Wanna do dinner and a show this weekend?" "Would you like to grab dinner tomorrow night?" "I heard you were sick, feeling better? Do you have plans Saturday?" "Want to get food and a movie this week?"
My roommates keep commenting on our 'dates'. We make plans for the next one while we are together practically. Sometimes we share popcorn or go out for ice cream. I've never dated anyone in my life, and I can only imagine that this is what it is like.
But he never says the word date. He's paid for dinner each of those nights, and I've had to fight to find something to pay for. I've been in love with him for five years, I want so badly for this to work. But I know what happened last time I broached the subject, and I really do enjoy our friendship. At the same time, though, I desperately want to reach out and grab his hand when we're sitting close in a dark theatre or riding in his car. Help?
I agree he's not that into you, not in that way, and that when a man really, truly is, a woman has trouble keeping him *off* her! (Hence one of the reasons why we need anti-stalking laws.)
I think maybe your friends are calling it 'dates' because of the effect each invitation has on *you*. Maybe you're putting a lot of effort into your 'getting ready' routine, like would a new and excited girlfriend... spending a lot of time preening in the bathroom, taking time and care over which outfit, looking very keen and expectant...that sort of thing? Because here's how it looks to me:
His reasons for having mainly stayed away (contact sporadic) included the fact the last meeting had turned awkward *plus* the fact he'd only just left further education to enter the wider world and was busy trying to get himself somewhat established. So when you nonetheless continued to show/reciprocate what he took as friendly interest, and then admitted you missed him, the established Just Friends context in which it got said meant it were the 'safer' (purely platonic) version of missing, meaning, it was now safe to develop the friendship to Bessie Mates level without constantly worrying whether you still had your romantic sights set on him and might proposition him again at any point. In other words, he's finally started to think of you as his very best friend and obviously puts a lot of time and attention into friendships he deems special and quite possibly life-lasting.
For that reason, I, personally, *wouldn't* confront him again if I myself valued his friendship, lest he came away with the conclusion that I were no friend, just someone who'd merely been biding my time under a more 'benign' cover, meaning, one-sided friendship in terms of genuine-ness, meaning, me having been the one leading *him* on for all that time.
You're obviously ripe for a relationship, though. So - what with that giving out a distinctive 'smell' (vibe) - I imagine you'll find yourself getting chatted-up quite soon. If/when it happens with someone you deem 'hotter than hot' then there's a danger of you suddenly losing all interest in your male friend or letting the friendship bit-by-bit peter out. And same for him if it happens to him. Plus there's the diplomacy element of his or your new squeeze not liking their lover having such a close friendship with a member of the opposite sex and - because of either of you appreciating 'which side your bread is buttered on' - either terminating the friendship or putting it on hold for quite a while. With this the case, assuming you do greatly value this guy's friendship, it would prove mightily convenient to either party concerned if he *were* gay.